Acetic Anhydride → N-(5-(6-(1-acetyl-pyrrolidin-2-yl)-2-pyridin-2-yl-1H-benzimidazol-5-yloxy)-pyridin-2-yl)-acetamide

HRID 13359

Reaction equation

HRID 13359 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[N:14]=[CH:13][C:12]([O:15][C:16]2[C:17]([CH:31]3[CH2:35][CH2:34][CH2:33][N:32]3[C:36](=[O:38])[CH3:37])=[CH:18][C:19]3[NH:23][C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)=[N:21][C:20]=3[CH:30]=2)=[CH:11][CH:10]=1>N1C=CC=CC=1>[C:36]([N:32]1[CH2:33][CH2:34][CH2:35][CH:31]1[C:17]1[C:16]([O:15][C:12]2[CH:11]=[CH:10][C:9]([NH:8][C:1](=[O:3])[CH3:2])=[N:14][CH:13]=2)=[CH:30][C:20]2[N:21]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)[NH:23][C:19]=2[CH:18]=1)(=[O:38])[CH3:37]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 231453671-(2-(6-(6-amino-pyridin-3-yloxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

Product 1

HCID 11190297N-(5-(6-(1-acetyl-pyrrolidin-2-yl)-2-pyridin-2-yl-1H-benzimidazol-5-yloxy)-pyridin-2-yl)-acetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.005 ml of acetic anhydride was added to a pyridine (1 ml) solution of 13.7 mg of 1-(2-(6-(6-amino-pyridin-3-yloxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone, and the reaction liquid was stirred at room temperature for 3 hours. The reaction liquid was evaporated away under reduced pressure, the resulting residue was dissolved in 1 ml of trifluoroacetic acid, and the reaction liquid was stirred at room temperature for 3 hours. The reaction liquid was distilled under reduced pressure, and the resulting residue was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid] and through silica gel column chromatography (developing solvent: chloroform/methanol=9/1) to obtain the entitled compound as an oily substance.

Workup

  1. customthe reaction liquid
  2. customThe reaction liquid
  3. customwas evaporated away under reduced pressure
  4. dissolutionthe resulting residue was dissolved in 1 ml of trifluoroacetic acid
  5. customthe reaction liquid
  6. stirringwas stirred at room temperature for 3 hours
  7. customThe reaction liquid
  8. distillationwas distilled under reduced pressure
  9. customthe resulting residue was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid] and through silica gel column chromatography (developing solvent: chloroform/methanol=9/1)
  10. customto obtain the entitled compound as an oily substance

Sources & evidence

ORD record
ord-418d477eaeb94b2faa09eaad87323df2
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Linked notes

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